The present invention relates to novel heterocyclic compounds, and more particularly to materials for light emitting devices that can convert electric energy to light to emit the light. The invention further relates to light emitting devices which can be suitably used in the fields of display elements, displays, back lights, electrophotography, illuminating light sources, recording light sources, reading light sources, indicators, signboards and interior decorations.
At present, the research and development of various display elements have been actively made. In particular, organic electroluminescence (EL) devices have attracted attention as promising display devices, because luminescence of high luminance can be obtained at low voltage. For example, a light emitting device in which an organic thin film is formed by vapor deposition of an organic compound (Applied Physics Letters, 51, 913 (1987)) has been known. The light emitting device described in this literature is substantially improved in light emitting characteristics compared with conventional monolayer elements, by using tris(8-hydroxyquinolinato)aluminum complex (Alq) as an electron transporting material and laminating a hole transporting material (amine compound) therewith.
As means for further improving the light emitting efficiency of the laminated light emitting devices, methods of doping the elements with fluorescent dyes have been known. For example, elements doped with coumarin dyes, described in Journal of Applied Physics, 65, 3610 (1989), are substantially improved in light emitting efficiency compared with elements not doped therewith. In this case, it is possible to take out light having a desired wavelength by changing the kind of fluorescent compound. However, when Alq is used as the electron transporting material, an increase in driving voltage for obtaining high luminance results in observation of green luminescence of Alq in addition to luminescence of the fluorescent compound used for doping. Accordingly, blue luminescence suffers from the problem of a reduction in color purity, so that the development of host materials which do not reduce the color purity has been desired. For improving this disadvantage, specified indole derivatives are disclosed in JP-A-10-92578 (the term xe2x80x9cJP-Axe2x80x9d as used herein means an xe2x80x9cunexamined published Japanese patent applicationxe2x80x9d) and U.S. Pat. No. 5,766,779. However, the compounds described therein have the problem that an increase in driving voltage is required for luminescence of high luminance. Accordingly, the development of compounds in which luminescence of high luminance is possible at low voltage has been desired.
As methods for increasing the light emitting efficiency, methods are reported in which hole blocking materials such as 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ) and bathocuproin (BCP) are used. However, the use of these known materials has raised a serious problem with regard to durability, particularly deterioration of the elements with time in storing at high temperatures in continuous luminescence.
The conventional elements good in color purity and high in light emitting efficiency are ones in which charge transporting materials are doped with fluorescent dyes in slight amounts, and have the problems that it is difficult to give the reproducibility of element characteristics from the production point of view, and that the long-term use thereof causes a reduction in luminance and changes in color because of low durability of the dyes. As means for solving the problems, the development of materials having both the charge transporting function and the luminescent function has been desired. However, the materials that have hitherto been developed have the problem that the use of fluorescent dyes at high concentrations results in difficulty in emitting light of high luminance by concentration quenching or association.
On the other hand, organic light emitting devices realizing luminescence of high luminance are elements in which organic materials are applied by vacuum deposition. The fabrication of the elements by coating is preferred from the viewpoints of simplification of manufacturing processes, processability and enlargement of area. However, the elements fabricated by the conventional coating -system are inferior in luminance and light emitting efficiency to the element fabricated by vapor deposition. It has been therefore a great problem to make it possible to emit light of high luminance at high efficiency.
It is therefore a primary object of the present invention to provide materials for light emitting devices good in light emitting characteristics and excellent in stability in repeated use thereof, and the light emitting devices. A secondary object of the present invention is to provide light emitting devices excellent in color purity, and materials for the light emitting devices making it possible. A third object of the present invention is to provide novel heterocyclic compounds effective in various electronic devices.
These objects have been attained by the following means:
(1) A material for a light emitting device consisting of a compound represented by the following general formula (I): 
xe2x80x83wherein A represents a heterocyclic group in which two or more aromatic heterocycles are condensed; m represents an integer of 2 or more, and the heterocyclic groups represented by A may be the same or different; and L represents a connecting group;
(2) A material for a light emitting device consisting of a compound represented by the following general formula (II): 
xe2x80x83wherein B represents a heterocyclic group in which two or more 5- and/or 6-membered aromatic heterocycles are condensed; m represents an integer of 2 or more, and the heterocyclic groups represented by B may be the same or different; and L represents a connecting group;
(3) A material for a light emitting device consisting of a compound represented by the following general formula (III): 
xe2x80x83wherein X represents O, S, Se, Te or Nxe2x80x94R; R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Q3 represents an atomic group necessary to form an aromatic heterocycle; m represents an integer of 2 or more; and L represents a connecting group;
(4) A material for a light emitting device consisting of a compound represented by the following general formula (IV): 
xe2x80x83wherein X represents O, S, Se, Te or Nxe2x80x94R; R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Q4 represents an atomic group necessary to form a nitrogen-containing aromatic heterocycle; m represents an integer of 2 or more; and L represents a connecting group;
(5) A material for a light emitting device consisting of a compound represented by the following general formula (V): 
xe2x80x83wherein X5 represents O, S or Nxe2x80x94R; R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Q5 represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; m represents an integer of 2 or more; and L represents a connecting group;
(6) A material for a light emitting device consisting of a compound represented by the following general formula (VI): 
xe2x80x83wherein X6 represents O, S or Nxe2x80x94R; R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Q6 represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; n represents an integer of 2 to 8; and L represents a connecting group;
(7) A material for a light emitting device consisting of a compound represented by the following general formula (VII): 
xe2x80x83wherein R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Q7 represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; n represents an integer of 2 to 8; and L represents a connecting group;
(8) A material for a light emitting device consisting of a compound represented by the following general formula (VIII): 
xe2x80x83wherein Q81, Q82 and Q83 each represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; R81, R82 and R83 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; L1, L2, and L3 each represents a connecting group; and Y represents a nitrogen atom or a 1,3,5-benzenetriyl group;
(9) A compound represented by the following general formula (IX): 
xe2x80x83wherein Q91, Q92 and Q93 each represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; and R91, R92 and R93 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group;
(10) A compound represented by the following general formula (X): 
xe2x80x83wherein R101, R102 and R103 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; R104, R105 and R106 each represents a substituent; and p1, p2 and p3 each represents an integer of 0 to 3;
(11) A material for a light emitting device consisting of a compound represented by the following general formula (XI): 
xe2x80x83wherein Q3 represents an atomic group necessary to form an aromatic heterocycle; R11 represents a hydrogen atom or a substituent; m represents an integer of 2 or more; and L represents a connecting group;
(12) A light emitting device comprising a light emitting layer or a plurality of organic compound films containing a light emitting layer formed between a pair of electrodes, wherein at least one layer is a layer containing at least one of the compounds represented by general formula (I) to (XI) described in (1) to (11);
(13) A light emitting device comprising a light emitting layer or a plurality of organic compound films containing a light emitting layer formed between a pair of electrodes, wherein at least one layer is a layer in which at least one of the compounds represented by general formula (I) to (XI) described in (1) to (11) is dispersed in a polymer;
(14) A light emitting device comprising a light emitting layer or a plurality of organic compound films containing a light emitting layer formed between a pair of electrodes, wherein at least one layer between the light emitting layer and a cathode is a layer containing at least one of the compounds represented by general formula (I) to (XI) described in (1) to (11);
(15) A light emitting device comprising a light emitting layer or a plurality of organic compound films containing a light emitting layer formed between a pair of electrodes, wherein at least one layer between a blue light emitting layer and a cathode is a layer containing at least one of the compounds represented by general formula (I) to (XI) described in (1) to (11); and
(16) A light emitting device comprising a light emitting layer or a plurality of organic compound films containing a light emitting layer formed between a pair of electrodes, wherein a layer containing at least one of the compounds represented by general formula (I) to (XI) described in (1) to (11) contains a blue light emitting material.
The invention will be described in detail below.
First, the compounds represented by general formula (I) will be described.
A represents a heterocyclic group in which two or more aromatic heterocycles are condensed. The heterocyclic groups represented by A may be the same or different.
The heterocyclic group represented by A is preferably a condensation product of 5- or 6-membered aromatic heterocycles, more preferably 2 to 6 aromatic heterocycles, still more preferably 2 or 3 aromatic heterocycles, and particularly preferably 2 aromatic heterocycles. In this case, the heteroatom is preferably an N, O, S, Se or Te atom, more preferably an N, O or S atom, and still more preferably an N atom.
The specific examples of the aromatic heterocycles constituting the heterocyclic groups represented by A include, for example, furan, thiophene, pyran, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, isothiazole, isoxazole, thiadiazole, oxadiazole, triazole, selenazole and tellurazole, preferably imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole and oxazole, and more preferably imidazole, thiazole, oxazole, pyridine, pyrazine, pyrimidine and pyridazine.
Specific examples of the condensed rings represented by A include, for example, indolizine, purine, pteridine, carboline, pyrroloimidazole, pyrrolotriazole, pyrazoloimidazole, pyrazolotriazole, pyrazolopyrimidine, pyrazolotriazine, triazolopyridine, tetraazaindene, imidazoimidazole, imidazopyridine, imidazopyrazine, imidazopyrimidine, imidazopyridazine, oxazolopyridine, oxazolopyrazine, oxazolopyrimidine, oxazolopyridazine, thiazolopyridine, thiazolopyrazine, thiazolopyrimidine, thiazolopyridazine, pyridinopyrazine, pyradinopyrazine, pyradinopyridazine, naphthyridine and imidazotriazine, preferably imidazopyridine, imidazopyrazine, imidazopyrimidine, imidazopyridazine, oxazolopyridine, oxazolo-pyrazine, oxazolopyrimidine, oxazolopyridazine, thiazolopyridine, thiazolopyrazine, thiazolopyrimidine, thiazolopyridazine, pyridinopyrazine and pyradinopyrazine, more preferably imidazopyridine, oxazolopyridine, thiazolopyridine, pyridinopyrazine and pyradinopyrazine, and particularly preferably imidazopyridine.
The heterocyclic group represented by A may be further condensed with another ring, and may have a substituent. The substituents of the heterocyclic groups represented by A include, for example, alkyl groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl and cyclohexyl), alkenyl groups (each having preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, such as vinyl, allyl, 2-butenyl and 3-pentenyl), alkynyl groups (each having preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, such as propargyl and 3-pentynyl), aryl groups (each having preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl and naphthyl), amino groups (each having preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino and ditolylamino), alkoxyl groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy and 2-ethylhexyloxy), aryloxy groups (each having preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy and 2-naphtyloxy), acyl groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, such as acetyl, benzoyl, formyl and pivaloyl), alkoxycarbonyl groups (each having preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl), aryloxycarbonyl groups (each having preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl), acyloxy groups (each having preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), acylamino groups (each having preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, such as acetylamio and benzoylamino), alkoxycarbonylamino groups (each having preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), aryloxycarbonylamino groups (each having preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino), sulfonylamino groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino), sulfamoyl groups (each having preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl and phenylsulfamoyl), carbamoyl groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl and phenylcarbamoyl), alkylthio groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio), arylthio groups (each having preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenylthio), sulfonyl groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl), sulfinyl groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl and benzenesulfinyl), ureido groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido and phenylureido), phosphoric acid amide groups (each having preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as diethylphosphoric acid amide and phenylphosphoric acid amide), hydroxyl, mercapto, halogen atoms (such as fluorine, chlorine, bromine and iodine), cyano, sulfo, carboxyl, nitro, hydroxamic acid groups, sulfino, hydrazino, imino, heterocyclic groups (each having preferably 1 to 30 carbon atoms, and more preferably 1 to 12 carbon atoms, having heteroatoms such as nitrogen, oxygen and sulfur, and specifically including imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl and benzthiazolyl, carbazolyl and azepinyl), and silyl groups (each having preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl and triphenylsilyl). These substituents may be further substituted. When there are two or more substituents, they may be the same or different. Further, they may be combined to form a ring if possible.
The substituents of the heterocyclic groups represented by A are preferably alkyl, alkenyl, alkynyl, aryl, amino, alkoxyl, aryloxy, acyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, -carbamoyl, alkylthio, arylthio, sulfonyl, cyano and heterocyclic groups and halogen atoms, more preferably alkyl, alkenyl, aryl, alkoxyl, aryloxy, cyano and heterocyclic groups and halogen atoms, still more preferably alkyl, aryl, alkoxyl, aryloxy and aromatic heterocyclic groups, and particularly preferably alkyl, aryl, alkoxyl and aromatic heterocyclic groups.
m represents an integer of 2 or more, preferably 2 to 8, more preferably 2 to 6, still more preferably 2 to 4, particularly preferably 2 or 3, and most preferably 3.
L represents a connecting group. The connecting group represented by L is preferably a single bond or a connecting group formed by C, N, O, S, Si or Ge, more preferably a single bond or a group comprising alkylene, alkenylene, alkynylene, arylene, a divalent heterocycle (preferably an aromatic heterocycle, and more preferably an aromatic heterocycle formed by an azole, thiophene or furan ring) or a combination thereof with N, and still more preferably a group comprising arylene, a divalent aromatic heterocycle or a combination thereof with N.
Specific examples of the connecting groups represented by L include, for example, the following groups, as well as a single bond. 
The connecting group represented by L may have a substituent. For example, the substituents of the heterocyclic groups represented by A can be applied as the substituents. The substituents of L are preferably alkyl, alkenyl, alkynyl, aryl, alkoxyl, aryloxy, acyl, cyano, heterocyclic and silyl groups and halogen atoms, more preferably alkyl, alkenyl, alkynyl, aryl, alkoxyl, aryloxy, cyano and aromatic heterocyclic groups and halogen atoms, and still more preferably alkyl, aryl and aromatic heterocyclic groups.
Of the compounds represented by general formula (I), preferred are compounds represented by the following general formula (II):
L"Parenopenst"B)mxe2x80x83xe2x80x83(II)
wherein m and L each has the same meaning as given for general formula (I), and each preferred range is also the same as given therefor; and B represents a heterocyclic group in which two or more 5- and/or 6-membered aromatic heterocycles are condensed, and the heterocyclic groups represented by B may be the same or different.
The heterocyclic group represented by B is preferably a condensation product of 2 to 6, 5- or 6-membered aromatic heterocycles, more preferably 2 or 3 aromatic heterocycles, and particularly preferably 2 aromatic heterocycles. In this case, the heteroatom is preferably an N, O, S, Se or Te atom, more preferably an N, O or S atom, and still more preferably an N atom.
Specific examples of the aromatic heterocycles constituting the heterocyclic groups represented by B include, for example, furan, thiophene, pyran, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, isothiazole, isoxazole, thiadiazole, oxadiazole, triazole, selenazole and tellurazole, preferably imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole and oxazole, and more preferably imidazole, thiazole, oxazole, pyridine, pyrazine, pyrimidine and pyridazine.
Specific examples of the condensed rings represented by B include, for example, indolizine, purine, pteridine, carboline, pyrroloimidazole, pyrrolotriazole, pyrazoloimidazole, pyrazolotriazole, pyrazolopyrimidine, pyrazolotriazine, triazolopyridine, tetraazaindene, imidazoimidazole, imidazopyridine, imidazopyrazine, imidazopyrimidine, imidazopyridazine, oxazolopyridine, oxazolopyrazine, oxazolopyrimidine, oxazolopyridazine, thiazolopyridine, thiazolopyrazine, thiazolopyrimidine, thiazolopyridazine, pyridinopyrazine, pyrazinopyrazine, pyrazinopyridazine, naphthilidine and imidazotriazine, preferably imidazopyridine, imidazopyrazine, imidazopyrimidine, imidazopyridazine, oxazolopyridine, oxazolo-pyrazine, oxazolopyrimidine, oxazolopyridazine, thiazolopyridine, thiazolopyrazine, thiazolopyrimidine, thiazolopyridazine, pyridinopyrazine and pyrazinopyrazine, more preferably imidazopyridine, oxazolopyridine, thiazolopyridine, pyridinopyrazine and pyrazinopyrazine, and particularly preferably imidazopyridine.
The heterocyclic group represented by B may have a substituent. As the substituents, the substituents of the heterocyclic groups represented by A in general formula (I) can be applied, and preferred substituents are also the same as given therefor.
Of the compounds represented by general formula (I), more preferred are compounds represented by the following general formula (III) or (XI): 
The compounds represented by general formula (III) will be explained.
In formula (III), m and L each has the same meaning as given for general formula (I), and each preferred range is also the same as given therefor; X represents O, S, Se, Te or Nxe2x80x94R; R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; and Q3 represents an atomic group necessary to form an aromatic heterocycle.
The aliphatic hydrocarbon groups represented by R are preferably alkyl groups (each having preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl and cyclohexyl), alkenyl groups (each having preferably 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms, such as vinyl, allyl, 2-butenyl and 3-pentenyl), alkynyl groups (each having preferably 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms, such as propargyl and 3-pentynyl). More preferred are alkyl groups and alkenyl groups.
The aryl groups represented by R each has preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-methoxyphenyl, 3-trifluoromethylphenyl, pentafluorophenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 1-naphthyl, 2-naphthyl and 1-pyrenyl.
The heterocyclic groups represented by R are monocyclic or condensed ring type heterocyclic groups (each having preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and still more preferably 2 to 10 carbon atoms), and preferably aromatic heterocyclic groups each containing at least one of nitrogen, oxygen, sulfur and selenium atoms. Specific examples of the heterocyclic groups represented by R include pyrrolidine, piperidine, pyrrole, furan, thiophene, imidazoline, imidazole, benzimidazole, naphthimidazole, thiazolidine, thiazole, benzthiazole, naphthothiazole, isothiazole, oxazoline, oxazole, benzoxazole, naphthoxazole, isoxazole, selenazole, benzoselenazole, naphthoselenazole, pyridine, quinoline, isoquinoline, indole, indolenine, pyrazole, pyrazine, pyrimidine, pyridazine, triazine, indazole, purine, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, phenanthridine, phenanthroline and tetraazaindene. Preferred are furan, thiophene, pyridine, quinoline, pyrazine, pyrimidine, pyridazine, triazine, phthalazine, naphthyridine, quinoxaline and quinazoline, more preferred are furan, thiophene, pyridine and quinoline, and particularly preferred is quinoline.
The aliphatic hydrocarbon group, aryl group and heterocyclic group represented by R may each have a substituent. As the substituents, the substituents of the heterocyclic groups represented by A in general formula (I) can be applied, and preferred substituents are also the same as given therefor.
R is preferably an alkyl group, an aryl group or an aromatic heterocyclic group, more preferably an aryl group or an aromatic heterocyclic group, and still more preferably an aryl group or an aromatic azole group.
X is preferably O, S or Nxe2x80x94R, more preferably O or Nxe2x80x94R, still more preferably Nxe2x80x94R, and particularly preferably Nxe2x80x94Ar (wherein Ar is an aryl group or an aromatic azole group, preferably an aryl group having 6 to 30 carbon atoms or an aromatic azole group having 2 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms or an aromatic azole group having 2 to 16 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms or an aromatic azole group having 2 to 10 carbon atoms).
Q3 represents an atomic group necessary to form an aromatic heterocycle. The aromatic heterocycle formed by Q3 is preferably a 5- or 6-membered aromatic heterocycle, more preferably a 5- or 6-membered nitrogen-containing aromatic heterocycle, and still more preferably a 6-membered nitrogen-containing aromatic heterocycle.
Specific examples of the aromatic heterocycles formed by Q3 include, for example, furan, thiophene, pyran, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, isothiazole, isoxazole, thiadiazole, oxadiazole, triazole, selenazole and tellurazole, preferably pyridine, pyrazine, pyrimidine and pyridazine, more preferably pyridine and pyrazine, and still more preferably pyridine.
The aromatic heterocycle formed by Q3may form a condensed ring with another ring, and may have a substituent. As the substituents, the substituents of the heterocyclic groups represented by A in general formula (I) can be applied, and preferred substituents are also the same as given therefor.
Of the compounds represented by general formula (III), still more preferred are compounds represented by the following general formula (IV): 
wherein m and L each has the same meaning as given for general formula (I), and each preferred range is also the same as given therefor; X has the same meaning as given for general formula (III), and a preferred range is also the same as given therefor; and Q4 represents an atomic group necessary to form a nitrogen-containing aromatic heterocycle.
The nitrogen-containing aromatic heterocycle formed by Q4 is preferably a 5- or 6-membered nitrogen-containing aromatic heterocycle, and more preferably a 6-membered nitrogen-containing aromatic heterocycle.
Specific examples of the nitrogen-containing aromatic heterocycles formed by Q4 include, for example, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, isothiazole, isoxazole, thiadiazole, oxadiazole, triazole, selenazole and tellurazole, preferably pyridine, pyrazine, pyrimidine and pyridazine, more preferably pyridine and pyrazine, and still more preferably pyridine.
The aromatic heterocycle formed by Q4 may form a condensed ring with another ring, and may have a substituent. As the substituents, the substituents of the heterocyclic groups represented by A in general formula (I) can be applied, and preferred substituents are also the same as given therefor.
Of the compounds represented by general formula (III), yet more preferred are compounds represented by the following general formula (V): 
wherein m and L each has the same meaning as given for general formula (I), and each preferred range is also the same as given therefor; X5 represents O, S or Nxe2x80x94R; R has the same meaning as given for general formula (III), and a preferred range is also the same as given therefor; and Q5 represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle.
Specific examples of the nitrogen-containing aromatic heterocycles formed by Q5 include, for example, pyridine, pyrazine, pyrimidine, pyridazine and triazine, preferably pyridine, pyrazine, pyrimidine and pyridazine, more preferably pyridine and pyrazine, and still more preferably pyridine.
The nitrogen-containing aromatic heterocycles formed by Q5 may form a condensed ring with another ring, and may have a substituent. As the substituents, the substituents of the heterocyclic groups represented by A in general formula (I) can be applied, and preferred substituents are also the same as given therefor.
Of the compounds represented by general formula (III), yet still more preferred are compounds represented by the following general formula (VI): 
wherein L has the same meaning as given for general formula (I), and a preferred range is also the same as given therefor; X6 has the same meaning as given for X5 in general formula (V), and a preferred range is also the same as given therefor; Q6 has the same meaning as given for Q5 in general formula (V), and a preferred range is also the same as given therefor; and n represents an integer of 2 to 8, preferably 2 to 6, more preferably 2 to 4, still more preferably 2 and 3, and particularly preferably 3.
Of the compounds represented by general formula (III), further preferred are compounds represented by the following general formula (VII): 
wherein L has the same meaning as given for general formula (I), and a preferred range is also the same as given therefor; R has the same meaning as given for general formula (III), and a preferred range is also the same as given therefor; Q7 has the same meaning as given for Q5 in general formula (V), and a preferred range is also the same as given therefor; and n has the same meaning as given for general formula (VI), and a preferred range is also the same as given therefor.
Of the compounds represented by general formula (III), still further preferred are compounds represented by the following general formula (VIII): 
wherein R81, R82 and R83 each has the same meaning as given for R in general formula (III), and a preferred range is also the same as given therefor; Q81, Q82 and Q83 each has the same meaning as given for Q5 in general formula (V), and a preferred range is also the same as given therefor; and L1, L2 and L3 each has the same meaning as given for L in general formula (I).
L1, L2 and L3 are each preferably a single bond, arylene, a divalent aromatic heterocycle or a connecting group comprising a combination thereof, more preferably a single bond, benzene, naphthalene, anthracene, pyridine, pyrazine, thiophene, furan, oxazole, thiazole, oxadiazole, thiadiazole, triazole or a connecting group comprising a combination thereof, still more preferably a single bond, benzene, thiophene or a connecting group comprising a combination thereof, particularly preferably a single bond, benzene or a connecting group comprising a combination thereof, and most preferably a single bond.
L1, L2 and L3 may each have a constituent. As the substituents, the substituents of the heterocyclic groups represented by A in general formula (I) can be applied.
Y represents a nitrogen atom or a 1,3,5-benzenetriyl group and the later may have substituents at positions 2, 4 and 6. Examples of the substituents include alkyl groups, aryl groups and halogen atoms. Y is preferably a nitrogen atom or an unsubstituted 1,3,5-benzenetriyl group, and more preferably an unsubstituted 1,3,5-benzenetriyl group.
Of the compounds represented by general formula (III), particularly preferred are compounds represented by the following general formula (IX): 
wherein R91, R92 and R93 each has the same meaning as given for R in general formula (III), and a preferred range is also the same as given therefor; and Q91, Q92 and Q93 each has the same meaning as given for Q5 in general formula (V), and a preferred range is also the same as given therefor.
Of the compounds represented by general formula (III), most preferred are compounds represented by the following general formula (X): 
wherein R101, R102 and R103 each has the same meaning as given for R in general formula (X), and a preferred range is also the same as given therefor; R104, R105, and R106 each represents a substituent, the substituents of the heterocyclic groups represented by A in general formula (I) can be applied as the substituents, and preferred substituents are also the same as given therefor; and p1, p2 and p3 each represents an integer of 0 to 3, preferably 0 to 2, more preferably 0 or 1, and still more preferably 0.
Next, general formula (XI) is described below. m and L each has the same meaning as given for general formula (I), and a preferred range is also the same as given therefor. Q3 has the same meaning as given for general formula (III), and a preferred range is also the same as given therefor. R11 represents a hydrogen atom or a substituent. Examples of the substituents represented by R11 include the substituents for the heterocyclic groups represented by A in general formula (I).
The substituents represented by R11 are preferably aliphatic hydrocarbon groups, aryl groups and aromatic heterocyclic groups; more preferably alkyl groups (each having preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms and particularly preferably 1 to 8 carbon atoms, and including, for example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl and cyclohexyl), aryl groups (each having preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms and particularly preferably 6 to 12 carbon atoms, and including, for example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-methoxyphenyl, 3-trifluoromethylphenyl, pentafluorophenyl, 1-naphthyl and 2-naphthyl), and aromatic heterocyclic groups (preferably aromatic heterocyclic groups each having preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms and still more preferably 2 to 10 carbon atoms, and more preferably aromatic heterocyclic groups each having at least one of nitrogen, oxygen, sulfur and selenium atoms, which include, for example, pyrrolidine, piperidine, pyrrole, furan, thiophene, imidazoline, imidazole, benzimidazole, naphth-imidazole, thiazolidine, thiazole, benzthiazole, naphtho-thiazole, isothiazole, oxazoline, oxazole, benzoxazole, naphthoxazole, isoxazole, selenazole, benzoselenazole, naphthoselenazole, pyridine, quinoline, isoquinoline, indole, indolenine, pyrazole, pyrazine, pyrimidine, pyridazine, triazine, indazole, purine, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, phenan-thridine, phenanthroline, tetraazaindene and carbazole, preferably furan, thiophene, pyridine, quinoline, pyrazine, pyrimidine, pyridazine, triazine, phthalazine, naphthyridine, quinoxaline and quinazoline, more preferably furan, thiophene, pyridine and quinoline, and still more preferably quinoline); and more preferably aryl groups and aromatic heterocyclic groups. The substituents represented by R11 may be further substituted, and may connect to form rings if possible.
Of the compounds represented by general formula (XI), more preferred are compounds represented by the following general formula (XII): 
wherein m and L each has the same meaning as given for general formula (I), and a preferred range is also the same as given therefor; Q12 has the same meaning as given for Q4 in general formula (IV), and a preferred range is also the same as given therefor; and R11 has the same meaning as given for general formula (XI), and a preferred range is also the same as given therefor.
Of the compounds represented by general formula (XI), still more preferred are compounds represented by the following general formula (XIII): 
wherein m and L each has the same meaning as given for general formula (I), and a preferred range is also the same as given therefor; Q13 has the same meaning as given for Q5 in general formula (V), and a preferred range is also the same as given therefor; and R11 has the same meaning as given for general formula (XI), and a preferred range is also the same as given therefor.
Of the compounds represented by general formula (XI) particularly preferred are compounds represented by the following general formula (XIV): 
wherein L1, L2, L3and Y each has the same meaning as given for general formula (VIII), and a preferred range is also the same as given therefor; Q141, Q142 and Q143 each has the same meaning as given for Q5 in general formula (V), and a preferred range is also the same as given therefor; and R141, R142 and R143 each has the same meaning as given for R11 in general formula (XI), and a preferred range is also the same as given therefor.
Of the compounds represented by general formula (XI), most preferred are compounds represented by the following general formula (XV): 
wherein Q151, Q152 and Q153 each has the same meaning as given for Q5 in general formula (V), and a preferred range is also the same as given therefor; and R151, R152 and R153 each has the same meaning as given for R11 in general formula (XI), and a preferred range is also the same as given therefor.
Specific examples of the compounds of the invention represented by general formula (I) are shown below, but it is to be understood that the invention is not limited thereto. 
The compounds of the invention represented by general formulas (I) to (XV) can be synthesized with reference to methods described in JP-B-44-23025 (the term xe2x80x9cJP-Bxe2x80x9d as used herein means an xe2x80x9cexamined Japanese patent publicationxe2x80x9d), JP-B-48-8842, JP-A-53-6331, JP-A-10-92578, U.S. Pat. Nos. 3,449,255 and 5,766,779, J. Am. Chem. Soc., 94, 2414 (1972), Helv. Chim. Acta, 63, 413 (1980) and Liebigs Ann. Chem, 1423 (1982).
Synthesis methods of the compounds of the invention are specifically illustrated below.